This paper assesses how the EU’s restrictive measures contribute to the enforcement of legal norms the EU considers to be essential. For the purpose of our analysis, we have chosen to focus on the measures in place against Russia since 2014 for its alleged violation of Ukraine’s territorial and sovereign integrity. By applying a so-called constructivist approach, we demonstrate that the restrictive measures have had a counterproductive effect because they contribute to the hostile relationship between the EU and Russia; each actor views the other as a threat and bases its response on this perception. Contrary to encouraging Russia to cease its policy in the Ukraine, the sanctions give Russia incentive to continue its actions in the region, which gives the EU incentive to pursue its sanctions policy, etc. We conclude that the EU should focus on tools that promote dialogue and communication, which would bridge the gap and help Russia no longer perceive the EU as a threat. This may then have the effect of encouraging Russia to demilitarize in Ukraine.